Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 21st October 2020 from 07:00 AM to 07:00 PM (BST).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 3, 2012
Previous Article Next Article

Natural polyphenols as safe alternatives to hydroquinone for the organocatalyzed reduction of dioxygen dissolved in water by diethylhydroxylamine (DEHA)

Author affiliations

Abstract

Reduction of dioxygen dissolved in water by diethylhydroxylamine (DEHA) in the presence of hydroquinones or quinones as organocatalysts is investigated with regard to reaction rate and catalyst turnover. Eleven p-benzoquinone derivatives bearing various electron-donating, electron-withdrawing and bulky substituents are studied. The catalytic activity of four benzenediols (hydroquinone, resorcinol, catechol and 4-tert-butylcatechol) and of four benzenetriols (hydroxyquinol, phloroglucinol, pyrogallol and 5-tert-butylpyrogallol) is compared. Mechanistic and kinetic studies indicate that the rate-determining step is the regeneration of hydroquinones through the reduction of the corresponding benzoquinones by DEHA. Then, eight natural polyphenols are tested as alternative catalysts to the potential carcinogen hydroquinone. Four of them (purpurin, myricetin, gallic acid and propyl gallate) exhibit some catalytic activity and gallic acid is shown to be even more efficient than hydroquinone itself. A further improvement of the catalytic system is achieved by adding catalase to disproportionate the generated hydrogen peroxide, which is detrimental for the catalyst. Thus, the oxygen scavenging system DEHA–gallic acid–catalase is found to be not only greener but also more efficient than the current system DEHA–hydroquinone since it gives water instead of hydrogen peroxide as the final reduction product of dioxygen.

Graphical abstract: Natural polyphenols as safe alternatives to hydroquinone for the organocatalyzed reduction of dioxygen dissolved in water by diethylhydroxylamine (DEHA)

Back to tab navigation

Supplementary files

Article information


Submitted
23 Nov 2011
Accepted
06 Jan 2012
First published
09 Feb 2012

Green Chem., 2012,14, 825-831
Article type
Paper

Natural polyphenols as safe alternatives to hydroquinone for the organocatalyzed reduction of dioxygen dissolved in water by diethylhydroxylamine (DEHA)

R. Lebeuf, Y. Zhu, V. Nardello-Rataj, J. Lallier and J. Aubry, Green Chem., 2012, 14, 825
DOI: 10.1039/C2GC16503A

Social activity

Search articles by author

Spotlight

Advertisements